Objective

To optimize the reaction from Exp099 to make this Ugi product using Mettler Toledo's automated Minimapper. Forty eight reactions are run in parallel using four reactant (2.0M in methanol) in different solvents / concentration.

Procedure

Make up 2M methanol solutions (25mL each) of starting materials - Furfurylamine (4.418mL), Boc-glycine (8.759g) and tert-butyl isocyanide (5.655mL) and 2.077M Benzaldehyde solution (5.275mL / 25mL methanol)
The following are added in this order in a reaction tube equipped with a filtration frit
1) The additional solvent (200uL methanol)
2) The benzaldehyde solution
3) The Furfurylamine solution
4) The Boc-Glycine solution
5) The tert-butyl isocycanide solution

Parameters to modify:
concentration - 0.5M, 0.25M and 0.1M
reagent excess - 1.0 and 1.2 equivalents
solvent (for 0.25 and 0.1 conc only): ethanol, acetonitrile, THF
Limiting reagent conc : 0.2mmol

This is 48 experiments total and they are listed in this spreadsheet

Map file ;

Results

Job file.

Discussion

Conclusion

The results are not meaningful because the liquid handler was not properly programmed.

Log

Log file1 ;

2008-07-11
19:05 Started the run with minimapper.
20:15 Minimapper completed the run.
20:20 Placed the miniblock (red) on the shaker

Tags

Compound	Inchi Key	Inchi
Furfurylamine	DDRPCXLAQZKBJP-UHFFFAOYAX	InChI=1/C5H7NO/c6-4-5-2-1-3-7-5/h1-3H,4,6H2
Benzaldehyde	HUMNYLRZRPPJDN-UHFFFAOYAE	InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H
tert-butylisocynide	FAGLEPBREOXSAC-UHFFFAOYAL	InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3
Boc-Glycine	VRPJIFMKZZEXLR-UHFFFAOYAN	InChI=1/C7H13NO4/c1-7(2,3)12-6(11)8-4-5(9)10/h4H2,1-3H3,(H,8,11)(​H,9,10)
Ugi Product	BXAOUWIVXLQYOZ-UHFFFAOYAZ	InChI=1/C24H33N3O5/c1-23(2,3)26-21(29)20(17-11-8-7-9-12-17)27(16- ​18-13-10-14-31-18)19(28)15-25-22(30)32-24(4,5)6/h7-14,20H,15-16H2​ ,1-6H3,(H,25,30)(H,26,29)